The year is 1942. Willie Morris (Frankie Muniz) is a shy and gawky eight-year-old living in the quiet town of Yazoo, Mississippi.
An only child, ignored at school and uncomfortable with girls, Willie looks up to and confides in next-door neighbour Dink Jenkins (Luke Wilson), the town’s star athlete, who is preparing to leave for military service. Willies father, Jack Morris (Kevin Bacon), a stern but good-hearted veteran who lost his leg in the Spanish Civil War, is chiefly responsible for Willies overprotective upbringing. Pushing in the other direction is his mother, Ellen Morris (Diane Lane), a capable woman who knows that what Willie needs most is some freedom, and a friend. Willies ninth birthday gives her an opportunity to offer him both, in the form of a Jack Russell terrier puppy that Willie names Skip. Skip's outgoing personality helps Willie in romance, and in friendship. But there are some problems that Skip cannot solve - and when Dink unexpectedly returns to town, Willie has a couple more tough lessons to learn about human nature.